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4-Isopropylaniline is a primary aromatic amine in which an isopropyl group is positioned para to the amino group. It is used mainly as a synthesis intermediate for substituted ureas, aryl isocyanates, agrochemical intermediates, colorants and specialty organic compounds. The product is normally supplied as a clear liquid whose color can range from colorless or pale yellow to brown because aromatic amines gradually discolor when exposed to air, light, heat or reactive metals.
CHEMICAL IDENTITY
Chemical name: 4-Isopropylaniline
IUPAC name: 4-(Propan-2-yl)aniline
CAS number: 99-88-7
EC number: 202-797-2
Molecular formula: C9H13N
Molecular weight: 135.21 g/mol
Structural formula: (CH3)2CHC6H4NH2
SMILES: CC(C)c1ccc(N)cc1
InChIKey: LRTFPLFDLJYEKT-UHFFFAOYSA-N
Common synonyms include p-Isopropylaniline, para-Isopropylaniline, 4-Aminocumene, p-Aminocumene, p-Cumidine, 4-Cumidine, 1-amino-4-isopropylbenzene and 4-(1-methylethyl)aniline. Because “cumidine” has also been used historically for other substituted anilines, the CAS number should be included in purchase orders, specifications and transport documents. The identity and principal synonyms are confirmed in the reference compound record.
PHYSICAL AND CHEMICAL PROPERTIES
4-Isopropylaniline is a liquid at normal room temperature. Representative values are a melting point of approximately -63°C, a boiling range of about 224–227°C, a density of approximately 0.95–0.99 g/cm³ and a refractive index near 1.54. The reference normal boiling point is approximately 498 K, or 225°C, according to the phase-change data record.
The material is practically insoluble in water but dissolves in many common organic solvents. Its flash point is reported between approximately 92°C and 116°C depending on the test method and data source. The value stated in the current lot-specific safety data sheet must therefore be used for risk assessment and equipment classification. Although its volatility is low at room temperature, hazardous vapors or aerosols can be generated during heating, spraying, vacuum-system discharge or open transfer.
4-Isopropylaniline has a characteristic aromatic-amine functionality and behaves as a weak organic base. It forms salts with mineral and organic acids and reacts readily with acylating, sulfonylating, carbamylating and isocyanate-forming reagents. Its theoretical amine value is approximately 415 mg KOH/g.
CHEMICAL FUNCTIONALITY
The primary amino group can undergo diazotization, acylation, alkylation, sulfonylation, condensation and conversion into urea, carbamate or isocyanate derivatives. Diazotization followed by coupling provides access to substituted azo compounds, while reaction with acid chlorides or anhydrides produces specialty anilides.
Conversion of 4-Isopropylaniline into 4-isopropylphenyl isocyanate creates a versatile route to substituted ureas and carbamates. The para-isopropyl group increases the hydrophobic character of downstream molecules and can modify their solubility, steric profile, crystallization behavior and compatibility with organic phases.
PRODUCTION
A conventional manufacturing route begins with nitration of cumene. Because direct nitration generally produces an isomer mixture, control and separation of the para-nitro isomer are important. The resulting 4-isopropylnitrobenzene is reduced to 4-Isopropylaniline by catalytic hydrogenation or, in older processes, by metal-and-acid reduction. A published process disclosure describes cumene nitration followed by reduction and separation to obtain para-isopropylaniline.
In catalytic manufacture, reduction passes through nitroso and hydroxylamine intermediates. Hydrogen uptake, reaction temperature and endpoint control are important for minimizing residual nitro compound, partially reduced intermediates and coupling products. After hydrogenation, the catalyst is removed and the crude amine is purified, commonly by vacuum distillation.
Potential process impurities include 4-isopropylnitrobenzene, ortho- and meta-isopropylaniline, aniline, cumene, nitroso or hydroxylamine intermediates, high-boiling condensation products, water and residual catalyst metals. Low-color material requires effective oxygen exclusion, suitable construction materials and controlled distillation conditions.
APPLICATIONS
Agrochemical and phenylurea intermediates
4-Isopropylaniline is associated with the synthesis of para-isopropylphenyl urea chemistry. It can be converted into 4-isopropylphenyl isocyanate and subsequently into substituted phenylureas, including intermediates related to isoproturon chemistry. It is also a recognized environmental transformation product of isoproturon and its demethylated metabolites, as documented in the agrochemical transformation record.
Pesticide-related use is subject to separate national registration and authorization requirements. Purchasing 4-Isopropylaniline does not authorize the manufacture, formulation or sale of a regulated active ingredient.
Aryl isocyanate and substituted urea synthesis
The amino group can be converted into the corresponding aryl isocyanate using controlled industrial chemistry. That intermediate reacts with amines or alcohols to form substituted ureas and carbamates. Moisture control is important because water consumes isocyanate groups and may generate carbon dioxide, insoluble ureas or pressure in closed equipment.
Dye and pigment intermediates
4-Isopropylaniline can be diazotized and coupled with activated aromatic compounds to prepare selected azo intermediates and colorants. The isopropyl substituent can influence hydrophobicity, shade, solvent compatibility and migration behavior. Amine purity, isomer distribution and color are important because trace impurities can change the hue and chromatographic profile of the finished colorant.
Pharmaceutical and fine-chemical synthesis
The product is a building block for research and industrial synthesis of substituted anilides, ureas, thioureas, imines and heterocyclic compounds. Application suitability depends on the impurity profile, residual metals and documentation requirements of the downstream process. Standard industrial material should not be represented as pharmaceutical grade unless it has been expressly manufactured and qualified for that purpose.
Analytical and environmental monitoring
High-purity 4-Isopropylaniline can be used as a reference material for developing GC or HPLC methods that monitor aromatic-amine intermediates and phenylurea transformation products in soil, water and industrial samples. Analytical-standard material requires assigned purity, traceability, defined storage conditions and a lot-specific expiry or retest period.
Research applications
4-Isopropylaniline is used as a substrate in reaction-development studies involving hydroamination, N-functionalization, catalytic coupling and aromatic-amine derivatization. Research-grade selection normally emphasizes identity, GC purity and spectroscopic conformity.
QUALITY PARAMETERS
Commercial grades commonly include technical or synthesis grade at approximately 98% minimum purity and high-purity material near 99%. Low-color, low-water and narrowly controlled isomer grades may be evaluated for sensitive synthesis.
Important purchasing parameters include GC assay, nonaqueous titration, appearance, color, water by Karl Fischer, amine value, density, refractive index and distillation range. Application-specific specifications may also cover residual 4-isopropylnitrobenzene, aniline, positional isomers, nonvolatile residue and catalyst metals.
Color alone is not a complete measure of purity because a product can darken through oxidation while retaining a high chromatographic assay. Nevertheless, color progression can indicate air exposure, unsuitable storage or trace-metal contamination and should be investigated for low-color applications.
PROCESSING CONSIDERATIONS
Closed charging and metering systems are recommended. Tanks, pumps, seals and hoses should be checked for compatibility with aromatic amines, and stainless steel or suitably lined equipment is generally preferred for controlled bulk handling. Contact with copper, brass, rust or incompatible elastomers should be evaluated because these materials can promote contamination, leakage or discoloration.
Use dry, oxygen-reduced equipment when color and stability are critical. Nitrogen blanketing can limit oxidative darkening, but confined-space and oxygen-deficiency procedures are required wherever inert gas is used. Equipment should be bonded and grounded when transferring the combustible liquid.
Reaction with strong acids can release substantial heat. Acid should be added under controlled cooling and agitation established by process-hazard evaluation. Diazotization requires strict temperature control and appropriate safeguards for unstable diazonium intermediates; dry diazonium salts should not be isolated. Isocyanate-forming routes involving highly toxic carbonylating agents must be conducted only in licensed, closed and specifically engineered facilities.
STORAGE AND HANDLING
Store in tightly closed, light-resistant containers in a cool, dry and well-ventilated area. Protect from air, direct sunlight, heat, ignition sources and moisture. Inert-gas filling may be appropriate for high-purity or low-color material. Keep separate from strong acids, strong oxidizing agents, acid chlorides and other incompatible reactive chemicals.
The storage area should have controlled access, spill containment and chemically resistant flooring. Do not eat, drink or smoke in handling areas. Workers should use chemical-resistant gloves selected from permeation data, protective clothing and splash goggles; a face shield should be added where splashing is possible. Local exhaust ventilation is required at charging, sampling and transfer points.
SAFETY AND HAZARD INFORMATION
Published classifications for 4-Isopropylaniline are not uniform. Aggregated European notifications predominantly identify skin irritation, serious eye irritation and respiratory-tract irritation, while some notifications also classify acute oral, dermal or inhalation toxicity. Other current safety data classify the material more severely for corrosivity, target-organ effects, suspected reproductive toxicity and aquatic toxicity. The variation is visible in the aggregated classification record.
The lot- and jurisdiction-specific Ataman Kimya safety data sheet must govern labeling, workplace controls and transport. Until the applicable classification is confirmed, the material should be handled conservatively as a harmful or potentially toxic aromatic amine capable of absorption through the skin. Aromatic-amine exposure may cause methemoglobinemia, reducing the blood’s ability to transport oxygen. Headache, dizziness, weakness, shortness of breath, confusion or blue coloration of the lips and nails requires immediate medical attention, even when symptoms are delayed.
Prevent all release to drains, soil and surface water. Waste, contaminated absorbents and empty uncleaned packaging should be managed as hazardous chemical waste in accordance with local regulations.
FIRST AID
Inhalation: Move the affected person to fresh air and keep them at rest in a position comfortable for breathing. Provide oxygen or respiratory support only through trained personnel. Obtain immediate medical advice if exposure is significant or any symptoms occur.
Skin contact: Remove contaminated clothing and footwear immediately. Rinse the skin thoroughly with water for at least 15 minutes. Do not use solvents to clean the skin. Obtain urgent medical attention, particularly if burning, discoloration or systemic symptoms develop.
Eye contact: Rinse cautiously with clean water for at least 15 minutes while holding the eyelids open. Remove contact lenses if this can be done easily, then continue rinsing. Obtain immediate medical examination.
Ingestion: Rinse the mouth. Do not induce vomiting and do not give anything by mouth to an unconscious person. Contact a poison center or physician immediately. Show the product label and safety data sheet to medical personnel.
FIRE AND SPILL RESPONSE
Suitable extinguishing media include alcohol-resistant foam, dry chemical, carbon dioxide and water fog selected for the surrounding fire. Do not direct a high-pressure water jet into spilled liquid. Fire may generate carbon monoxide, carbon dioxide, nitrogen oxides and other hazardous decomposition products. Firefighters require positive-pressure self-contained breathing apparatus and full protective clothing.
For a spill, isolate the area, eliminate ignition sources and ventilate from a safe location. Personnel entering the area should wear chemical-resistant protection appropriate to the applicable SDS. Stop the leak only when this can be done safely, protect drains, absorb the liquid with a compatible inert material and place the waste in closed, labeled containers. Large spills require specialist emergency response and environmental notification where applicable.
TRANSPORT INFORMATION
Some current transport classifications assign 4-Isopropylaniline to UN 2735, AMINES, LIQUID, CORROSIVE, N.O.S., Class 8, with packing group II or III depending on the classification and shipped material. Other classifications may differ. Marine-pollutant status can also depend on the environmental classification adopted for the shipment.
The correct UN number, proper shipping name, packing group, labels and documentation must be determined from the current Ataman Kimya SDS, product concentration, package size, transport mode and destination-country regulations. Do not assign transport status solely from the flash point or chemical name.
PACKAGING AND SUPPLY
4-Isopropylaniline can be evaluated for supply in suitable bottles, drums, intermediate containers or bulk arrangements according to quantity, product specification and transport requirements. Light-resistant, tightly sealed packaging with inert-gas protection may be selected where color stability is important. UN-approved packaging is used when required by the applicable transport classification.
Ataman Kimya can coordinate assay, water, color, isomer profile, residual nitro compound, packaging and documentation requirements before order confirmation. A certificate of analysis, safety data sheet and available technical or regulatory documentation can be provided for the contracted grade.
For specifications, samples, packaging options and commercial inquiries, contact Ataman Kimya.
Phone: +90 216 577 10 10
Email: info@atamankimya.com
